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Winter Garden › Oakland Area

The Oakland Area of Winter Garden

Oakland area of Winter GardenKnown as one of the hidden gems of Florida, Oakland is surrounded by moss-draped oak trees and found on the shores of Lake Apopka. It's a naturally beautiful area of Winter Garden boasting waterfront properties within a serene setting nestled in the Northwestern area of Winter Garden just before Clermont off Hwy 50 in West Orange County.

The Oakland Nature Preserve

One of the best attractions found in Oakland is the Oakland Nature Preserve. Since 1999, this preserve has been providing education to visitors about the native flora and fauna, while providing conservation efforts for the area land. Its open year-round and there's no charge to enjoy the preserve.

Oakland Nature Preserve TrailThe Nature Preserve provides plenty of fun with 128 acres of space for environmental education and recreation. It's a popular spot for field trips and summer camps. Many visitors come for the guided tours, hiking trails and special events.

The Boardwalk also attracts many visitors. It's the most popular trail on the preserve and takes you through shaded wetlands to a covered pavilion with views of Lake Apopka. Interpretive signage is found throughout to identify trees and plants. Often, you will spot turtles, alligators and wading birds from the Boardwalk.

Lake Apopka

Another huge part of the culture and recreation of Oakland, Florida is Lake Apopka. It's the second largest lake in the entire state and used to be known as the bass fishing capital of the entire southern United States. The lake is fed by a natural spring and covers about 30,800 acres of surface area.

The Oakland Heritage Festival

Old Mansion in Oakland FloridaOne of the largest and most popular events held annually in Oakland is the Heritage Festival. This festival provides plenty of fun with more than 2,000 attendees and over 50 vendors every year. It's held at Speer Park in Oakland and helps to support the Oakland Nature Preserve.

Those attending the event get to enjoy hayride tours, a silent auction, boat tours, live music, a number of great speakers, a petting zoo and so much more. There are crafts and activities specifically for children and even some of the more exotic animals on hand. The festival is held in October every year.

Oakland Avenue Charter School

Along with the beautiful nature of the area, Oakland, Florida is home to a 700-student charter elementary school. This school provides a choice for residents with school-aged children outside of the public schools serving the community.

New construction in Oakland Florida

Real Estate in Oakland

A variety of housing options are found in Oakland with homes ranging from about $200K up to more than $1 million. The area does have some undeveloped land for those looking to create a new construction home and there are plenty of waterfront homes and lots available, as well.

Some of the finer waterfront estates provide incredible views of Lake Apopka and may even provide private docks. Oakland attracts a variety of home buyers due to the range of options and prices.

Neighborhoods in the Oakland Area include:Oakland Park neighborhood in the Oakland area of Winter Garden

  • Deer Island
  • Downtown Oakland
  • Hull Island
  • Johns Cove
  • Johns Landing
  • Longleaf at Oakland
  • Oakland Hills
  • Oakland Park
  • Oakland Trails
  • Trailside Station
  • Tucker Oaks
  • Verde Park

Oakland Florida Homes for Sale

0001 Tucker Oaks Boulevard, Winter Garden image
0001 Tucker Oaks Boulevard, Winter Garden $11,000,000

Pre-Construction. To be built. Future Medical, Profesional Office and Retail Plaza to feature a mixture of office and retail spaces. A project of over48,000 sqf. of buil...

  • Tucker Oaks SubDv.
  • 34787 Zip Code
16250 W Colonial, Winter Garden image
16250 W Colonial, Winter Garden $2,900,000

COMMERCIAL 5 (+-) ACRES DIRECT HWY 50 FRONTAGE. SEE SURVEY IN PHOTOS, HIGH TRAFFIC AREA WITH RED LIGHT AND ROAD ON EACH SIDE. GROWTH AREA WITH MANY OPPORTUNITIES, FUTUR...

  • 34787 Zip Code
16251 W Colonial Drive, Oakland image
16251 W Colonial Drive, Oakland $2,400,000 ▲

PRIME LOCATION HWY 50 FRONTAGE. This C-1 Zoned 3.52 +/- acres is right near the border of booming Winter Garden (population 48,000) and just East of Clermont (population ...

  • 34760 Zip Code
703 Large Oak Lane, Winter Garden image
703 Large Oak Lane, Winter Garden $1,745,000

Pre-Construction. To be built. Pre-Construction. To be Built. Here is your chance to design and build your dream CUSTOM MODERN FARMHOUSE in one Winter Gardens Premier co...

  • 4 Beds
  • 5 Baths
  • Oakland Hills SubDv.
  • 34787 Zip Code
15198 E Oakland Avenue, Winter Garden image
15198 E Oakland Avenue, Winter Garden $1,599,000 ▲

Pre-Construction. To be built. Fall in love with this modern farmhouse masterpiece within Winter Garden’s premier luxury new home community, Oakland Hills! Unlike anythin...

  • 4 Beds
  • 4 Baths
  • Oakland Hills SubDv.
  • 34787 Zip Code
800 Hull Island Drive, Oakland image
800 Hull Island Drive, Oakland $1,495,000 ▼

These five plus acre are adjacent to a newly developed area of homes ranging in the 400,000 value. The property sits at the end of a cul-de-sac within this development. T...

  • 34787 Zip Code
750 Hull Island Drive, Oakland image
750 Hull Island Drive, Oakland $1,295,000 ▼

These six plus acre are adjacent to a newly developed area of homes ranging in the 400,000 value. The property sits at the end of a cul-de-sac within this development. Th...

  • 34787 Zip Code
255 Deer Isle Drive, Winter Garden image
255 Deer Isle Drive, Winter Garden $1,100,000

Located in the highly sought-after Deer Island community, this pool home gives you incredible panoramic lake views from the front yard as well as the back! The property i...

  • 4 Beds
  • 2.5 Baths
  • Deer Island SubDv.
  • 34787 Zip Code
1033 Britton Alley, Winter Garden image
1033 Britton Alley, Winter Garden $879,900 ▼

Price Reduced! Welcome home to this beauty in Oakland Park. Featuring 4 Bedrooms, 3.5 Bathrooms, soft light walls, plantation shutters and hand scraped hardwood floors t...

  • 4 Beds
  • 3.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
1254 Civitas Way, Winter Garden image
1254 Civitas Way, Winter Garden $863,620

Under Construction. Contemporary design and classic appeal blend to create the brilliant Seaside dream home plan. Your open floor plan provides a sensational expanse of e...

  • 4 Beds
  • 3.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
1207 Saddleback Drive, Winter Garden image
1207 Saddleback Drive, Winter Garden $822,210

Under Construction. You'll be delighted by the glamorous comforts and attention to detail that makes The Shoreline a remarkable new home plan. Put your interior design sk...

  • 4 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
1213 Union Club Drive, Winter Garden image
1213 Union Club Drive, Winter Garden $799,900

Beautiful custom built 3/2.5 home by award winning J&J Building. This POOL home is located in the highly sought after Oakland Park community! The Craftsman style home is ...

  • 3 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
979 Huntspoint Street, Winter Garden image
979 Huntspoint Street, Winter Garden $799,000 ▼

Picture-perfect farmhouse in the PARADE of HOMES winning community, Oakland Park! Located just footsteps to PARKS, trails, water views, the resort style POOL and clubhou...

  • 4 Beds
  • 3 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
1065 Kershaw Drive, Winter Garden image
1065 Kershaw Drive, Winter Garden $799,000 ▼

This PARK front home in OAKLAND PARK is just footsteps away from the LAKEFRONT walking trail, Community Clubhouse, and RESORT style POOL! The model features 4 bedrooms (m...

  • 4 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
1316 Southern Sun Drive, Oakland image
1316 Southern Sun Drive, Oakland $793,460 ▼

Under Construction. The Newcastle, a beautiful new home for sale in Oakland, is as flexible as it is beautiful featuring a front covered porch and 3-car tandem garage. Wi...

  • 5 Beds
  • 4 Baths
  • Hull Island SubDv.
  • 34787 Zip Code
1364 Foltz Loop, Oakland image
1364 Foltz Loop, Oakland $767,550 ▼

Under Construction. The Newcastle offers a welcoming front porch. Once inside you will be welcomed to a high ceiling foyer. This home offers 3562 sf with 5 spacious bedro...

  • 5 Beds
  • 4 Baths
  • Hull Island At Oakland SubDv.
  • 34787 Zip Code
1429 Eastover Loop, Winter Garden image
1429 Eastover Loop, Winter Garden $750,000 ▼

PARK FRONT CUSTOM MANOR HOME WITH A EUROPEAN FLAIR IN OAKLAND PARK. One of a kind, FGBC certified green Manor Home with 2,378 square feet and finishes that would rival an...

  • 3 Beds
  • 3.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
924 Civitas Way, Winter Garden image
924 Civitas Way, Winter Garden $750,000

*** 24 hour notice to view at request of the Seller *** Take a stroll into Oakland Park where you'll find this gem of a home, located one block from the state-of-the-art ...

  • 3 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
1328 Foltz Loop, Oakland image
1328 Foltz Loop, Oakland $710,260 ▼

Under Construction. This new home in Oakland is a single-story, 3-way-split plan with 4 bedrooms and 3 baths. Find a bedroom with its own full bath right off the foyer at...

  • 4 Beds
  • 3 Baths
  • Hull Island SubDv.
  • 34787 Zip Code
402 Largovista Drive, Oakland image
402 Largovista Drive, Oakland $704,900 ▼

Nestled in one of Central Florida's most desirable lakefront gated communities, John's Landing sits a custom luxury lakeview home measured at 4,470 total square feet. Thi...

  • 3 Beds
  • 2.5 Baths
  • Johns Landing Ph 01 44/47 SubDv.
  • 34787 Zip Code
410 E Henschen Avenue, Oakland image
410 E Henschen Avenue, Oakland $700,000

Located in the town of Oakland, which is nestled in between Clermont and Winter Garden, sits this beautiful pool home with a detached guest house with NO HOA and solar pa...

  • 5 Beds
  • 4 Baths
  • Starr Gardens Oakland SubDv.
  • 34760 Zip Code
17946 Hither Hills Circle, Winter Garden image
17946 Hither Hills Circle, Winter Garden $674,990 ▲

Under Construction. Under Construction! Stunning Summerlin floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85...

  • 5 Beds
  • 4.5 Baths
  • Lake Apopka Sound SubDv.
  • 34787 Zip Code
17942 Hither Hills Circle, Winter Garden image
17942 Hither Hills Circle, Winter Garden $645,990 ▼

Under Construction. Under Construction! Stunning Portland floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...

  • 4 Beds
  • 3.5 Baths
  • Lake Apopka Sound SubDv.
  • 34787 Zip Code
1301 Johns Cove Lane, Oakland image
1301 Johns Cove Lane, Oakland $640,000

Large 4 Bedroom 2 Bathroom 3-way split floor plan with an Office and a 2 car Garage. Exclusively located in a gated community with easy access to Florida's Turnpike, 408,...

  • 4 Beds
  • 2 Baths
  • Johns Cove 43/104 SubDv.
  • 34787 Zip Code
14425 Shaman Way, Winter Garden image
14425 Shaman Way, Winter Garden $630,990

Under Construction. Under Construction! Stunning Portland floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...

  • 4 Beds
  • 3.5 Baths
  • Lake Apopka Sound SubDv.
  • 34787 Zip Code
17922 Hither Hills Circle, Winter Garden image
17922 Hither Hills Circle, Winter Garden $624,990

Under Construction. Stunning Camden floor plan located in the highly sought after community of Lake Apopka Sound. Featuring a rare Multi-Generational site with a private ...

  • 4 Beds
  • 3.5 Baths
  • Lake Apopka Sound SubDv.
  • 34787 Zip Code
17938 Hither Hills Circle, Winter Garden image
17938 Hither Hills Circle, Winter Garden $620,990 ▼

Under Construction. Stunning Camden floor plan located in the highly sought after community of Lake Apopka Sound. Featuring a rare Multi-Generational site with a private ...

  • 4 Beds
  • 3.5 Baths
  • Lake Apopka Sound SubDv.
  • 34787 Zip Code
229 Largovista Drive, Oakland image
229 Largovista Drive, Oakland $609,990 ▼

Come live in one of Central Florida's most desirable lakefront gated communities, John's Landing. This amazing 5 bedroom, 4 bath home with double car garage, brand new do...

  • 5 Beds
  • 4 Baths
  • Johns Landing Ph 02 48 138 SubDv.
  • 34787 Zip Code
17934 Hither Hills Circle, Winter Garden image
17934 Hither Hills Circle, Winter Garden $580,990

Under Construction. Charming Destin floor plan located in the highly sought after community of Lake Apopka Sound. This open design concept offers ample entertaining and l...

  • 4 Beds
  • 3 Baths
  • Lake Apopka Sound SubDv.
  • 34787 Zip Code
17930 Hither Hills Circle, Winter Garden image
17930 Hither Hills Circle, Winter Garden $565,990 ▼

Under Construction. Under Construction! Stunning Robinson floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...

  • 4 Beds
  • 3 Baths
  • Lake Apopka Sound SubDv.
  • 34787 Zip Code
14417 Shaman Circle, Winter Garden image
14417 Shaman Circle, Winter Garden $555,990

Under Construction. Under Construction! Stunning Robinson floor plan located in the highly sought after community of Lake Apopka Sound. All homesites are oversized at 85'...

  • 4 Beds
  • 3 Baths
  • Lake Apopka Sound SubDv.
  • 34787 Zip Code
1071 Stationside Drive, Oakland image
1071 Stationside Drive, Oakland $550,000

Totally renovated 3 bedroom, 2 bathroom home located in the heart of Oakland with private sweeping views of the nature preserve! This home has brand new flooring througho...

  • 3 Beds
  • 2 Baths
  • Trailside Station Rep 44/23 SubDv.
  • 34787 Zip Code
2490 Standing Rock Circle, Oakland image
2490 Standing Rock Circle, Oakland $550,000 ▼

Why wait to build? This home is ready for you now! Located in one of Oakland's premier communites, Oakland Trails is the perfect spot to call home. With 3 bedrooms, 2.5...

  • 3 Beds
  • 2.5 Baths
  • Oakland Trails Ph 1 SubDv.
  • 34787 Zip Code
917 Mckinnon Square, Winter Garden image
917 Mckinnon Square, Winter Garden $524,730

Under Construction. The Kelsey new home plan combines elegance, comfort, and top-quality craftsmanship. Escape to the serenity of your Owner’s Retreat, which includes a c...

  • 3 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
921 Mckinnon Square, Winter Garden image
921 Mckinnon Square, Winter Garden $515,720

Under Construction. Elegance and sophistication combine with the genuine comforts that make each day delightful in The Summerton lifestyle home plan. The versatile upstai...

  • 4 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
2724 Bobcat Chase Boulevard, Oakland image
2724 Bobcat Chase Boulevard, Oakland $477,900 ▼

Welcome to this LIKE NEW home located in the desirable town of Oakland. This spacious home offers 3 bedrooms, 2.5 bathrooms, an open floor plan, beautiful kitchen with gr...

  • 3 Beds
  • 2.5 Baths
  • Longleaf At Oakland SubDv.
  • 34787 Zip Code
1961 Standing Rock Circle, Oakland image
1961 Standing Rock Circle, Oakland $469,500

PREMIER COMMUNITY! Welcome to Oakland Trails, a community in Oakland, Florida, situated right off of the Florida Turnpike! This 3 bed/2.5 bath home situated on a corner l...

  • 3 Beds
  • 2.5 Baths
  • Oakland Trails Ph 2 SubDv.
  • 34787 Zip Code
267 Deer Isle Drive, Winter Garden image
267 Deer Isle Drive, Winter Garden $449,900

Exclusive Deer Island Gated Community - Waterfront Homesite - with incredible views and private boat dock capability on John’s Lake. Why settle for as-built when you can...

  • Deer Island SubDv.
  • 34787 Zip Code
2208 Gopher Tortoise Terrace, Oakland image
2208 Gopher Tortoise Terrace, Oakland — 2208 $420,000

LOCATED NEAR DOWNTOWN WINTER GARDEN, CLOSE TO THE WINTER GARDEN TRAIL, PLANT STREET, TURNIPIKE AND MUCH MORE. HOUSE OFFERS A 3 BEDROOMS AND 2 AND 1/2 BATH WITH LOTS OF UP...

  • 3 Beds
  • 2.5 Baths
  • Longleaf/Oakland Rep SubDv.
  • 34787 Zip Code
1206 Scarlet Oak Loop, Winter Garden image
1206 Scarlet Oak Loop, Winter Garden — 1206 $402,000 ▼

One or more photo(s) has been virtually staged. Built in 2014, this Winter Garden two-story home offers granite countertops, and a two-car garage.

  • 3 Beds
  • 2.5 Baths
  • Villas/Tucker Oaks SubDv.
  • 34787 Zip Code
1511 Sweet Apple Street, Oakland image
1511 Sweet Apple Street, Oakland — N/A $399,500

Welcome home to this beautiful 3 bed, 2.5 bath, nearly new, townhome property in sought after Oakland/Winter Garden area, in Longleaf at Oakland community. As you approac...

  • 3 Beds
  • 2.5 Baths
  • Longleaf/Oakland Rep SubDv.
  • 34787 Zip Code
210 W Sadler Avenue, Oakland image
210 W Sadler Avenue, Oakland $364,900 ▼

***Price Reduction*** New low price makes this a must see today! Great single-family home with metal roof sits on a large corner lot on a tree lined street in the desirab...

  • 4 Beds
  • 1.5 Baths
  • Oakland Town SubDv.
  • 34760 Zip Code
1364 Scarlet Oak Loop, Winter Garden image
1364 Scarlet Oak Loop, Winter Garden $354,900

Welcome home to this STUNNING townhome with a full 2-car GARAGE in the sought-after neighborhood of Tucker Oaks. Live close to downtown Winter Garden without the massive ...

  • 3 Beds
  • 2.5 Baths
  • Villas/Tucker Oaks SubDv.
  • 34787 Zip Code
15304 Oak Apple Court Unit 12C, Winter Garden image
15304 Oak Apple Court Unit 12C, Winter Garden — 12 $329,900

This home is in great condition and is move in ready! Only 3 units per building in the Condos part of the Tucker Oaks Gated community. Just off SR-50 w/easy access to 5 D...

  • 3 Beds
  • 2.5 Baths
  • Tucker Oaks SubDv.
  • 34787 Zip Code
1404 Avalon Road, Winter Garden image
1404 Avalon Road, Winter Garden $238,000 ▲

Huge residential lot in desirable Winter Garden. Lot is located in a quiet unpaved road with a ranch type home as your only neighbor. Back part of lot overlooks virgin wo...

  • Acreage SubDv.
  • 34787 Zip Code
Live Oak, Winter Garden image
Live Oak, Winter Garden $210,000 ▼

DON’T MISS THIS RARE OPPORTUNITY! Winter Garden Residential corner Lot in Highly Desirable John Lake Homesites. Build your dream home with a beautiful view of Johns Lake...

  • Johns Lake Homesites Add 01 SubDv.
  • 34787 Zip Code
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Realtor David MyersDavid Myers 407-801-3286
Your Winter Garden Real Estate Expert

Winter Garden Areas

  • Downtown Winter Garden
  • Horizon West
  • Oakland
  • Winter Garden Village

Downtown Winter Garden Area Neighborhoods

  • Downtown Winter Garden
  • Brandy Creek
  • Chapin Station
  • Courtlea Oaks
  • Courtlea Park
  • Covington Chase
  • Crown Point Springs
  • Daniels Crossing
  • Fullers Crossing
  • Fullers Landing
  • Heritage at Plant Street
  • Island Pointe
  • Kings Bay
  • Lake Cove Pointe
  • Lakeview Reserve
  • Magnolia Wood
  • McAllister Landing
  • Oakglen Estates
  • Oaks at Brandy Lake
  • Park Place
  • Regal Pointe
  • Stanton Estates
  • Sterling Pointe
  • Timbercreek Pines
  • Traditions
  • Trails of Winter Garden
  • Tuscany
  • Walkers Grove
  • Winter Oaks

Winter Garden Village Area Neighborhoods

  • Alexander Ridge
  • Amberleigh
  • Avalon Reserve
  • Avalon Ridge (NEW)
  • Banana Bay Estates
  • Bay Isle
  • Belle Meade
  • Black Lake Park
  • Black Lake Preserve
  • Bradford Creek
  • Bronsons Landing
  • Canopy Oaks
  • Carriage Pointe
  • Cobblestone
  • Country Lakes
  • Cypress Reserve
  • Daniels Landing
  • Deerfield Place
  • Emerald Ridge
  • Foxcrest
  • Glynwood
  • Grove Park
  • Grovehurst
  • Hickory Hammock
  • Johns Lake Pointe
  • Lake Roberts Landing
  • Orange Cove
  • The Orchard
  • Oxford Chase
  • Regency Oaks
  • Reserve at Carriage Pointe
  • Roper Reserve
  • Sanctuary at Twin Waters
  • Southern Pines
  • Stone Creek
  • Stoneybrook West
  • Sunset Lakes
  • Tilden Place
  • Twinwaters
  • Waterside
  • Westfield Lakes
  • Windermere Crossing
  • Windward Cay
  • Wintermere Harbor
  • Wintermere Pointe
  • Woodbridge on the Green

Horizon West Area Neighborhoods

  • Avalon Cove
  • Cove At Hamlin
  • Enclave at Hamlin
  • Encore at Ovation
  • Hamilton Gardens
  • Hamlin Reserve
  • Hawksmoor
  • Highland Ridge (NEW)
  • Highlands Summerlake
  • Independence
  • Isles Of Lake Hancock
  • Lake Hancock Preserve
  • Lakeshore
  • Lakeside at Hamlin
  • Lakeview Pointe
  • Lakeview Preserve
  • Latham Park
  • Mezzano (NEW)
  • Orchard Hills
  • Orchard Park
  • Osprey Ranch (NEW)
  • Overlook At Hamlin
  • Panther View
  • Ravenna
  • Sanctuary at Hamlin
  • Storey Grove
  • Summerlake
  • Summerlake Groves
  • Waterleigh
  • Watermark
  • Westhaven Ovation (NEW)
  • Wincey Groves
  • Winding Bay

Oakland Area Neighborhoods

  • Deer Island
  • Downtown Oakland
  • Hull Island
  • Johns Cove
  • Johns Landing
  • Longleaf at Oakland
  • Oakland Hills
  • Oakland Park
  • Oakland Trails
  • Trailside Station
  • Tucker Oaks
  • Verde Park

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